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Stereoselectivity in 6-halopenicillanate grignard reactions
Affiliation:1. Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium;2. Peoples’ Friendship University of Russia (RUDN University) Miklukho-Maklaya street 6, 117198 Moscow, Russia;1. School of Statistics, Dongbei University of Finance and Economics, Dalian 116025, China;2. School of Statistics, Jiangxi University of Finance and Economics, Nanchang 333000, China;3. School of Economics and Management, Dalian University of Technology, Dalian 116025, China.;1. School of Public Administration, Southwestern University of Finance and Economics, Chengdu, China;2. Plymouth Business School, University of Plymouth, Plymouth, United Kingdom;3. School of Statistics and Applied Mathematics, Anhui University of Finance and Economics, Bengbu, China;4. School of Public Finance and Taxation, Southwestern University of Finance and Economics, Chengdu, China
Abstract:Structural modifications of 6-halopenicillanate Grignards result in increased “aldol” stereoselectivity. The intermediacy of tetrahedral penicillin carbanions in THF and β-lactam enolates in CH2Cl2/toluene is proposed.
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